5-Chloro-6-hydroxynicotinoyl chloride → HCID 178467206, compound

HRID 981325Notes

Reaction equation

HRID 981325 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[C:12]([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C>O1CCCC1>[OH:11][C:3]1[C:2]([Cl:1])=[CH:10][C:6]([C:7](=[O:8])[CH3:12])=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 1785211275-Chloro-6-hydroxynicotinoyl chloride

Product 1

HCID 178467206HCID 178467206, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

7.2 g (37.5 mmol) of 5-chloro-6-hydroxynicotinoyl chloride in 10 ml of absolute tetrahydrofuran are added to a boiling solution of 8.55 g (37.5 mmol) of diethyl ethoxymagnesium-malonate (prepared in accordance with Org. Synth. Coll. Vol. IV (1963), 285) in 120 ml of absolute tetrahydrofuran and the mixture is heated under reflux for 2 hours. After neutralization with 2N sulphuric acid, the organic phase is separated off and evaporated. The residue is heated under reflux in a mixture of 30 ml of glacial acetic acid, 20 ml of water and 5 ml of concentrated sulphuric acid for 4 hours. The mixture is stirred into ice-water, brought to pH 4 and extracted with ethyl acetate. Drying and evaporation gives 6 g (93%) of the title compound, melting point: 188° to 189° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customAfter neutralization with 2N sulphuric acid, the organic phase is separated off
  4. customevaporated
  5. temperatureThe residue is heated
  6. temperatureunder reflux in a mixture of 30 ml of glacial acetic acid, 20 ml of water and 5 ml of concentrated sulphuric acid for 4 hours
  7. extractionextracted with ethyl acetate
  8. customDrying
  9. customevaporation

Sources & evidence

ORD record
ord-c059db1bb1f64a3c91a9cb54679e494e
Source dataset
uspto-grants-1991_02
Patent number
US04990620

Reaction notes

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